Aromatic and Cyclic Cationic Surfactants
BRU CE R. BA ILEY III Akzo Chemicals Inc., The McCook Research Center, McCook, Illinois
I. Introduction 188
II. Unsaturated Heterocyclic Compounds 188 A. Pyridinium derivatives 188 B. Quinolinium derivatives 197 C. Isoquinolinium derivatives 200 D. Benz-X-azolium derivatives 201 E. Imidazolium derivatives 203 F. Oxazolinium derivatives 203 G. Pyrimidinium derivatives 204
III. Saturated Heterocyclic Compounds 205 A. Piperidinium derivatives 205 B. Morpholinium derivatives 205 C. Piperazinium derivatives 209 D. Pyrrolidinium derivatives 209 E. Hexahydroazepinium derivatives 210 F. Oxazinium derivatives 211
IV. Fluorinated Heterocyclic Compounds 211 A. Synthesis 211
Notes 215 References 215
This chapter covers the synthesis and reactions of surface-active ammonium compounds in which the nitrogen atom carrying the positive charge is part of a heterocyclic ring. The information contained in this chapter was taken from the literature covering the period 1969-1987. Because of the large amount of work done with imidazolinium quaternaries, the chemistry of these materials is covered separately in Chapter 3. The present chapter is organized into three main sections. The first section deals with unsaturated and aromatic compounds. The second section covers saturated cyclic materials. The third section contains a discussion of the preparation of cationic surfactants that contain perfluoroalkyl side chains. The discussion of each class of materials (i.e., morpholinium derivatives) is divided into two subsections. The first subsection is a discussion of the synthetic methods used to prepare a particular class of surfactants; the second deals with reactions of the surfactants. Since many of the synthetic methods were found in the patent literature and often cover several classes of materials, these synthetic methods are discussed in the section where specific examples were given for the method. In general, only representative examples and general applications are given for any particular material.